


Valentines Day Ain't For Spiders

by Mystery_Name



Category: Deadpool - All Media Types, Spider-Man - All Media Types
Genre: Cuddles, Cute, F/M, Fluffy, No Smut, Penny Parker - Freeform, Very fluffy, deadpool be a helpless romantic, i have no idea where this is headed, ideas are appreciated, making it up as I go, no lemon cause i don't write that, peter parker!female, spiderman!female
Language: English
Status: Completed
Published: 2015-08-29
Updated: 2016-02-15
Packaged: 2018-04-17 18:40:18
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 8,876
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4677167
Author URL: https://archiveofourown.org/users/Mystery_Name/pseuds/Mystery_Name
Summary: <blockquote class="userstuff">
              <p>Penny Parker/Spider-Girl never really like Valentines day. Maybe it was because of all the chubby, half-naked cupid babies shooting arrows at people, or the fact that she was usually alone on said holiday. </p><p>Either way, her view on the 'Day of Love' is about to change when someone starts leaving her little presents around New York, and sending her on a scavenger hunt that will sure to lead her to figuring out she's not alone as she thought...maybe she'll even get a boyfriend out of the experience. ;)</p>
            </blockquote>





	1. Valentine's Day? No thanks!

**Author's Note:**

> Hope you enjoy.

Valentine’s Day. 

The holiday of lovers. Aphrodite’s fun day. Cupids running wild. All the flowers, chocolates, and cheap little gives to symbolize a person love for another. A day where no one is alone, a day where they and their significant other can openly express their affection without being told “There are children here!”

But not for Penny Parker. 

She’s never really liked Valentine’s Day, come on, a day to show your lover how much you love them. Can’t you show them your love every day? Do they have to make a certain holiday just for romance? It could be the fact that Penny thought you should express your affection for those you care about EVERY day. 

Or it could be because she’s always alone on Valentine’s Day.

Either way, skateboarding down the streets of New York while ignoring the disgusting window displays of baby’s in diapers assaulting two poor people with arrows, or the bouquet of roses she’ll never receive, Penny made her way home from a grueling day of school. 

21 and still going to College, you would think she’d have a boyfriend. Penny didn’t why she could never get a guy to notice her. Maybe it was because she was always so buried in studying? Or taking pictures for the Daily Bugle to help pay her rent? Because she had short hair (cut to her jawline) and a nerd? Or was it saving the city from muggers and villains who threatened civilian safety?

Oh, that might be it. 

No one would have guessed, nerdy Penny Parker was the web-slinging, crime fighting vigilante of New York known as Spider-Girl. 

But still…  
Penny continued to ignore the displays, disgust had become a permanent expression on her face for the last few days. It was bad enough watching Flash Thompson and his girlfriend make-out in front of her locker, now they make-out in front of her locker without a teacher pulling them apart because it was “Valentine’s Day”, and they were “Just expressing each other’s love”.

Yuck! 

Penny finally made it to her apartment building, she took an elevator up to her floor, and hurried onto her apartment.   
It was a pretty decent size, a living room, kitchen, bathroom, and bedroom, not to mention a few closets here and there. Jonah’s paychecks were barely enough to keep her here. But it was home sweet home. 

She dropped her backpack on the couch, her skateboard on the floor, kicked her shoes off and fixed herself a sandwich before relaxing on the couch. At least in the privacy in her own home she didn’t have to hear about Valentine’s Day.   
As long as she was in her apartment, it wasn’t even a holiday. 

Until the sound of sirens outside caught her ears. Penny groaned, but got up. She discarded her long-sleeved shirt, pants, and socks and in their place she wore a spandex, blue and red suit with black web designs, and a black spider symbol on the chest. Penny grabbed her mask, gloves, and web shooter from her backpack, pulled them on, and was out of the apartment before anyone could say: Spider-Girl. 

Penny shot strand after strand of webs, following the sound of sirens. She stopped on a building, perched on the edge and gazed down to see what the ruckus was about. It was a car chase, 5-6 police cars were in pursuit of a cheap, black convertible with a guy hanging half-way out shooting at the cops with a pistol. 

Penny, now Spider-Girl, dived off the buildings, swung on a few webs before landing on the hood of the car. The guy hanging out nearly fell out on the street from surprise. “What was that?!” she heard his partner inside demand. 

“Spider-Girl!?” the guy said, both answering his partner in a panicked tone, and to Penny. He was wearing a cheap. Black cloth mask with the eyes and mouth cut out. 

“Spider-Girl, at your service.” Penny said, giving the guy a mock bow. “Okay not really YOUR service, more to the service of the people, but you get the idea.” 

The masked guy looked inside briefly, “What do I do?!” he asked. 

“Shoot her!” his partner cried, but by the time the guy looked back up Penny had already webbed the guy’s gun away, and delivered a swift punch in his jaw. The guy gave a cry of pain and fell fully out of the car, but before his body could hit the pavement, Penny grabbed his shirt and threw him over to the sidewalk. In midair she shot another web and stuck him to the building wall. 

A police car stopped its chase to go get the guy in custody. The guy’s partner, inside the car driving clutched the bag of money they stole tightly, with his other hand gripping the wheel. It was quiet on the roof of his car; he heard no steps or voices.   
His eyes flitted left and right, sweat and sprung up on his forehead. “Awww, do I make you nervous?” Penny said suddenly from the seat next to him. 

The guy cursed, and jerked from surprise, sending the car flying around in the street. “Whoa, whoa, whoa. I know I usually get that kind of reaction from a guy, but yeesh!” Penny said, wrestling the wheel from the guy. 

Civilians scrambled out of the way outside, a women was pushed to the street from the panicked crowds, and her husband hurried down to help her back up. 

It would have been adorable, if it wasn’t Valentine’s Day, and if it wasn’t right in front of the rampaging car. Penny’s eyes widened, and with a mighty jerk she veered the car out of the way just in time, but sent them sailing into another car, and flipping them upside down in an alleyway. 

The guy forced his door open, he didn’t even grab the stolen money, he just booked it down the alleyway. Penny sighed in exasperation; she pulled herself from the wreckage and swung after the guy. He wasn’t even half way down the alley before a web stuck him on the back and pulled him backward. 

“Do you know how much easier it would be if you guys just stayed put?” Penny told him. The guy struggled to get away, yelling at her to let him go. “They never learn.” She says to herself, as she spins him into a cocoon and sticking him by the wrecked car.   
The guy yelled in frustration when he couldn’t break free of the sticky white substance. “Who fights crime on Valentine’s Day anyway the guy said, more to himself than Penny. “I thought Spider-Girl would be with….Spider-MAN or something!” the guy said, more to Penny than himself now, only succeeding in reminding Penny how alone she was today.

“Who robs a store on Valentine’s Day?” Penny retorted, and for good measure she webbed him over the mouth. The police had swarmed the scene by then, and got to work cleaning the wreckage, getting the convict, and retrieving the stolen money.   
Penny was about to sling away, but was interrupted by “Spider-Girl! Wait!” she stopped and turned around. A young police officer ran toward her, he was handsome with buzz cut blonde hair, and deep brown eyes. 

“Yes?” Penny asked.

“I was told to give this to you, the next time I saw you.” He said, handing her two roses. One was red, the other blue and they were tied together with a black ribbon, and a card was tied to the ribbon with a white string. 

Penny looked at it in surprise, “I’ve always wondered if you had a boyfriend.” The police officer smiled, “Now I know you do.”

“I do?” Penny asked, holding the roses like they were about to explode. 

The police officer gave her a confused look, “Y-yeah…at least I thought….” He cleared his throat uncomfortable, and excused himself. 

“Wait!” Penny stopped him, he looked back at her, “Who are these from?” she asked. 

The guy smiled again, “I’m not supposed to tell.” He says, and is gone before she says anything else. Confused, Penny looks back at the roses and web slings to a high building, away from all chaos. She looks at them more closely, the red rose was a deep, rich color, and the blue rose was a soft, light color. Both stems were long, with emerald leaves bursting out, but the thorns had been cut off. 

Penny opened up the card; there were three words on it: Empire State Building. 

The words were written in with a blue sharpie, in sloppy cursive, there was a red heart in the corner. Penny read the card two more times, just to make sure her eyes weren’t tricking her, before web-slinging toward the Empire State Building.


	2. Who?

**Notes for the Chapter:**

> Hope you enjoy!

Chapter 2-  
Penny swung over to the Empire State Building, she had webbed the rose to her arm as she was web-slinging. The tall building drew closer, and with one mighty swing Penny was at the very top, holding on to the tall rod. She wearily looked around, her spider-sense wasn’t tingling, so she wasn’t in any immediate danger. And the rest of the roof of the building looked deserted.  
“So I was stood up?” Penny asked herself, “Or did I stood them up? Er…stand them up? Hm...how would you say that?” Realizing she was talking to herself again, Penny quickly restricted all thoughts to stay in her head. 

Was she supposed to go INSIDE the building? Even if she did, where was she supposed to go? She might get some funny looks if she entered the lobby in her spidey costume. Penny debated one whether she should leave or not before something white caught her attention. 

She jumped down to see a folded piece of paper taped to the ground. It was addressed as: In case Spidey fails to see why she is here. Once again it was in a sloppy cursive, and written in blue marker. Carefully, Penny picked the tape off and opened it.  
Two words were on it: Look up. 

She did. 

And that’s when she spotted something hanging at the very top of the rod. She swung up there, and landed right by it.  
It was another rose, only a red one, but it had a blue ribbon tied on it, and as before the thorns were cut off and a paper was hanging from a white string. Penny opened it, and read the card. Another location was printed on it: Central Park.  
Penny took the roses off her arm, and added the new rose. 

She webbed it back to her arm and went off to Central Park. As always, the park held people picnic’ing on the grass, rolling down the skating trails, although today is seemed especially full. With couples walking down the decorated trails of hearts and flowers, holding hands, or laying next to each other on the grass talking softly and chuckling, or perhaps even kissing.  
In any other case Penny would’ve hi-tailed it out of there, but not today. She was on a mission. Somewhere in this park, there was probable another rose.

Penny was smart; she saw a pattern going on. 

But she wasn’t smart enough to know the roses exact location in the park. Where to look? Penny swung on a tree, and peered curiously around the park. 

“Come out, come out little rose.” She mumbled to herself. 

Sadly, the rose remained hidden. Penny jumped from tree to tree, looking around the park like some deranged spider-monkey. Ha, spider-monkey. It was when she had wondered somewhere around the center of the park when someone called out to her, holding a familiar rose in their hand. 

Penny landed in front of them, it was a girl with blonde hair, she had her arm snaked around a guy by her. It was obvious they were out together, “Here,” the girl said, handing Penny the rose, this one was blue with the black ribbon and card hanging down. “I was told to give it to you once I saw you.” The girl explained. 

“Do you know who’s leaving these for me?” Penny tried, but like the police officer, the guy replied “Sorry, we’re not supposed to tell.”

The girl smirked at Penny, “I’ve always wondered what a hero’s love life was like,” she said, “It’s kind of interesting.” 

Penny only shrugged, “I don’t know about love life.” She mumbled. 

“Please,” the girl said, “whoever that guy is that wanted us to give you this; he obviously cares about you enough to do this. Anyway, I’d love to chat, but Jakes taking me to the movies.” The girl smiled at the guy, Jake I guess, who nodded in agreement.  
They wave before walking away, Penny stood there for a moment, going over what they said, before realizing that her presence was drawing attention and slung into a tree for some cover. Leaning against a branch she opened the new card, with once again a location on it: The Brooklyn Bridge. 

Adding it to her ever-growing bouquet of flowers, Penny swung from tree to tree, out of the Park, and toward the bridge.  
Her thoughts wondered to whoever these flowers were from. Could it be the Sinister 6? Penny was pretty sure they were still in prison, she probable would have heard about it if there was a jail break. So was it independently planned? Was something setting her up to go to all these places and end up being surprised attacked? Are they distracting her so they can pull a bank heist, and she’ll be clear across New York to not stop it? 

But then again, if one of the villains she fought was doing this, the flowers probable wouldn’t be so delicately decorated and placed. Penny could tell from the way the thorns were neatly cut off, and how perfectly straight the bow was that these flowers were done careful, and neatly. If Rhino was behind this, he probably wouldn’t have sent the flowers, and only the thorns. Or if Mysterio decided to play around, it probably would be done sloppily, the villains hated her a lot, and Penny doubted they’d take the time to actually make this look nice. 

But then again, Doc Ock was pretty sneaky, maybe it’s his plan. 

Penny thought about just ditching the hunt, and heading home. She was pretty sure there were some reruns of Friends playing on TV, it would be so easy to just drop the flowers and leave. But once the Brooklyn Bridge appeared from above and behind buildings, Penny’s thoughts of leaving left without her, and she was filled with curiosity.  
Who is dedicated enough to actually do all this for her?

Be it a villain, or random citizen, Penny would just keep her eyes open, and her spider-sense ready. She may be as curious as a kitten, but this kitten (or spider) is ready to fight fist and webs incase this turned out to be a trap.  
So she swung onto the bridge, and kept an eye open for danger, but also for another rose. She was half-way across the bridge when she spotted a rose, delicately taped to one of the platforms above the bridge. Penny landed on the platform, and picked up the rose, and reading the card, with its new location: Avengers Tower. 

That brought new ideas. Was this from the Avengers? It was highly doubtful, seeing as the well-known heroes hardly glanced in her direction when she was around. Maybe they were playing a trick? Like a newbie hero welcome tradition. Have the newbie go on a scavenger hunt across town, bring them back to the tower and dump ice cold water on them. 

“Ah shoot!” Penny cursed, swing back across the bridge, heading for Avengers Tower. “I’m probably the worst hero out there.”  
But she couldn’t help. She needs to know who’s behind this, someone evil, or someone good. 

She was going to get to the bottom of this.


	3. Penny Webs Tony In the Mouth

**Summary for the Chapter:**

> The chapter title is pretty self-explanatory.

It wasn’t long before the Avengers tower rose above the buildings like a beacon; Penny found it weird that even though you couldn’t see the superheroes inhabiting the tower, you could feel them. Like an invisible force that just hits you and you can just feel the power and authority they had, it was rather intimidating. Penny wasn’t surprised that no villain had tried infiltrate it or blow it up, well-besides Red Skull and maybe a couple of those other ‘high top’ villains Penny didn’t fight.

She stopped on the building nearest to the tower and examined the outside as best she could, she hoped that the rose was on the outside somewhere. Penny didn’t think she could go in and face the Avengers, sure they were super heroes like her, but they were worldly known, people liked them, they had money, and they have a Norse god on their side. While Penny was known throughout New York and Manhattan, she was constantly picked on by a cranky newspaper (*cough Jameson cough*) with a weird mustache, she could barely pay the rent for her apartment, and she was in the superhero business alone.

Yep, not intimidating at all.

And yes, that entire statement was sarcastic.

So she scanned the building from the bottom to the top-there! At the very top of Avengers tower on the gigantic A, Penny could barely detect something small and red on it.

She thwipped her webs and was off, it wasn’t long before she landed on the A. Carefully she untapped the layers of tape that secured it, but before she could open the card her spidey sense tingled and before she knew it there were dozens of high-tech guns pointed at her.

Penny didn’t know what else to do beside hold her hands up in surrender and say, “AH! I come on peace!”

A robotic, but surprisingly sophisticated, voice said, “ _Mr. Stark requests that who so ever is sticking to his tower better get off by the count of 10_.” The voice started counting down, “Okay, okay!” Penny said, “I’m going.”

She held out her hand to thwip away, but a voice above stopped her, “Hey J.A.R.V.I.S you didn’t say the intruder was Spider-Girl.” Penny looked up to see the handsome face of Anthony Start AKA Tony Stark AKA Iron Man leaning over the giant balcony, looking at her.

Penny swallowed hard.

“ _Forgive me Sir, but you did say the threaten them, without asking who the intruder was_.” The voice said, J.A.R.V.I.S, replied.

Tony waved it off, “Whatever, tell me next time.”

“ _Very good, Sir_.” J.A.R.V.I.S said, there was a few clicks and groans before all the guns were gone and Penny’s spider-sense finally stopped doing a tap-dance in her brain. Penny was sure what to do, so she simple waved to Tony while saying, “Er…thanks.”

“No problem,” Tony smiled, “J.A.R.V.I.S can be a bit rational sometimes.” Though Penny distinctly remembered the A.I saying Tony had ordered it to threaten her, but Penny decided not to point out that fact.

Penny scratched her neck awkwardly, “Well, I guess I’ll be going then.” She tried to web-sling away again, but once again Tony interrupted. “Actually, while you’re here I was wondering if I could talk to you.” Penny felt her throat go dry.

She tried to say something, “Well..erm…I was actually…” Tony noticed the rose in her hand and realization struck him and he smirked.

“So you’re the girl he was prattling on about.” Tony chuckled, “It makes sense why he was putting a rose this high up on my building.” Penny forgot about her nervous brain at the mention of ‘he’, the guy she had been wondering about this entire time.

Penny climbed up to face Tony, who was a little intrigued by her wall-climbing, like he was analyzing her and trying to figure out how she did it. “Who is ‘he’?” she asked. Tony looked surprised Penny didn’t know, “You mean you haven’t figured it out yet?” Penny couldn’t help but blush under mask, was this ‘admirer’, if that was the case, really that obvious.  She couldn’t help but feel a little stupid, even though she didn’t have anything to feel embarrassed about.

She shook her timidly, Tony shrugged  and Penny leaned further, “I think you deserve to know, ‘he’ is D-“ but Penny was actually surprised when she instead webbed Tony’s mouth shut.

“Never mind!” she burst out, but then blushed even harder. She had just webbed TONY STARK, IRON MAN, IN THE MOUTH! Oh she was so sued. Both screwed, and sued! “I am so sorry.” Penny apologized as Tony struggled with ripping the substance off his face.

She wanted to offer to help him take it off, but blushed harder when she realized how weird that sounded, and decided to just mentally bang her head on the tower until she lost consciousness. She hid her face in her one of her hands as Tony got the last of it off, “That’s one way to quiet a person.” He mumbled to himself.

“Sorry,” Penny apologized again, “I guess I decided I don’t want you to tell me who ‘he’ is, so I panicked and just-“ Penny made a thwip gesture, “and-ah gosh I’m sorry.”

Tony simply chuckled, “No harm done I suppose,  but are you sure you don’t want to know, I mean this guy is really crazy, like crazy enough to climb up my tower and tape a rose to it. I was so close to blasting him to smithereens until he pleaded for me to keep it there.” Tony smirked, “He told me he was  trying to ‘woo the girl of his dreams’, I was kind of curious to who D-I mean ‘he’ was interested in. I’m kind of surprised.”

Penny couldn’t help but feel a little offended, “Why?” she asked, but it came out a bit more harsh than intended.

Tony held his hands up in surrender, “I just meant I didn’t think you were his type.” Penny calmed down a little, “But are you sure you don’t want to know?” Tony asked again, “I know you’re new to this whole…hero gig and you don’t those kind of people as much as others do, but it stills worries me a little, you seem like a good person.”

Penny didn’t know whether to be offended or flattered, so she just stuck with holding her arms over her chest casually, as if she didn’t care what he though. “I’ll be fine,” Penny assured. Though Tony didn’t look convinced.

But finally she simple shrugged in defeat, “Fine, but I want you to take something before you go.” He said walking inside the tower. Penny wasn’t sure what she was supposed to do, was she supposed to go in, was she supposed stay outside…

Thankfully Tony came out a moment later holding a small, black chip. It had two buttons at the top, a red one and a blue one. Tony handed it to Penny, who took it hesitantly. “Don’t worry, it won’t harm you.” Tony reassured her at seeing her hesitance, “But it will tell me if you’re in danger or not, the red one means your okay, the blue means you’re in danger. Press either one when you meet him, the Avengers will be there before you can say: Valentine’s Day.”

Penny looked back at the chip and nodded, “But,” she said, “I though the red one usually meant danger, and blue was okay.”

“Psh, I never follow the rules.” Tony smirked. But Penny was confused, Tony barely knew her and he was already looking out for her. Why? Tony seemed to read her thoughts, “I know it seems strange of me for doing this,” he told her, “but-well, we heroes look out for each other. I’ve seen what you’ve been doing out there Spider-Girl, your doing really good. Sure we Avengers save the world, but its heroes like you that save the people worth saving the world for….Does that make sense?”

In it way, it did. The Avengers faced world-threatening problems, like Ultron, Loki, and aliens. Penny saved people from muggers, stopped bank heists and car chases. She saved everyday people, the very people the Avengers work to protect. Without the people there’s no point in protecting the Earth. Penny nodded, “Yeah that makes sense.”

“Good, because Cap is so much better at explaining those deep, sentimental things. Anyway you better get going, remember red is good, blue is bad.” Penny nodded, “Be careful.” Tony added.

Penny couldn’t help but roll her eyes, “Yes dad.” She said sarcastically. Tony smiled again, Penny shot a web, but once again she was interrupted when Tony grabbed her arm, “And,” he said, “if you ever shoot that web-stuff in my eyes again, I’ll sue you.” He was serious, but a look of mischief still shone in his eyes. Penny chuckled awkwardly, “Yeah, okay.” She agreed.

Tony nodded and let go, Penny swung off till the Avengers tower fell behind. She knew one thing about her ‘admirer’ his name started with a D, according to Tony anyway. Penny was kind of surprised when he had stopped Tony from telling who D was (she decided to just call him D, instead of ‘he’), but she found that she wanted to find out on her own. Now though she wasn’t as worried if it turned out to be a trap, Tony had given her the black chip. If it turned to trouble, simply push the red button-er blue button, and she’d have the Avengers as back-up. Kind of exciting really.

But there was still on thing that bugged her, (haha bugged), Tony seemed truly worried, he didn’t seem to trust D. Whoever can make Iron Man uneasy must be quite a character, Penny stopped on a building and held the rose in her hand.

Was she doing the right thing? Was she really put herself at a great risk? For a moment she debated on just dropping the rose to the streets below and never sees it again, just go home and forget all this, maybe save her from pain or embarrassment.

What was she supposed to do?

But looking back down at the rose, how carefully the thorns were cut off, the neatness of the bow, the attempted neatness of the writing, it all intrigued her. Who was doing this? Did they really care for her? What did Tony say? He said D was trying to ‘woo’ her, maybe it was working. Penny did feel a little wooed.

She stared at the card, a mental battle raging through her head. Curiously she opened it to see the next address:  _The_ _Daily Bugle_.

A small thought spiked Penny’s mind, was this a trick from the Bugle? But she quickly dismissed the idea, J.J didn’t seem like the kind of person who would do this. The idea of him at his desk with a basket of red and blue roses, and hand written cards in stacks, as he carefully snipped on the thorns on the roses gave her cognitive dissonance. It just didn’t seem right.

Clutching the rose a little tighter, Penny added it to her collection carefully and sighed deeply, “I officially, completely, 100% despise, loath, and hate Valentine’s Day!” Penny stated, but none-the-less started toward the Daily Bugle.

**Notes for the Chapter:**

> I hope it didn't seem too OCC. Tony just seemed like he would worry about Penny if she was following around a guy she didn't even know, and if he couldn't talk her out of it, then just give her something so she could get help if she needed it.   
> Besides I kind of wanted some super family added in there, just excluding Cap. 
> 
> Don't worry, if any of you thought Tony showed any kind of romantic interest in her, your wrong, he only worries for a new, young hero, that is all. 
> 
> I hope you enjoyed it!


	4. P.S I Am Not A Stalker

Penny landed on the Daily Bugle building, and looked around its exterior for any signs of a rose. She kind of hoped no one saw her up here, especially Mr. Hitler Mustache himself; she honestly didn’t need any more crap from J.J than she already had. So she tried to be discreet, even snuck around quietly as if someone would hear her. But her luck was horrible, as usual, and the cranky newspaper man in all his Spider-Girl hating glory, popped his head out a window and yelled at her to ‘get off his building before he calls the cops’ and ‘how she didn’t value private property’ which honestly was ridiculous-it a bulding for goodness sakes! Penny ignored him as best she could, not in the mood to get in an argument-though she was surprised to how loud J.J could yell. She was pretty high up, and she still heard him loud and clear. Yikes!

Until Jameson mentioned another red-clad freak climbing up his building, which spiked Penny’s curiosity. She climbed down next to Jameson who glared at her with a face that could rival the Goblins. “So, this red-clad freak you mentioned. Did he happen to leave anything-I don’t know a rose perhaps-lying around anywhere?” Penny asked innocently.

Jameson scoffed, “You mean the other freak climbing up my building besides you?” Jameson demanded, “How am I supposed to know, and even if I did I wouldn’t tell you! It could be a bomb, for all I know, meant to kill me!”

Penny rolled her eyes, “Believe pickle-puss, you’re not that important.” J.J grit his teeth, and proceeded to yell in her ear before Penny finally spotted the rose. This one was blue, and neatly done like the others. The only bad thing, it happened to be in Jameson’s office, on his desk, under a few papers. He didn’t know about-yeah right! J.J noticed where Spider-Girl seemed to be staring, and narrowed his eyes. “Just get off my building you wall-crawling weirdo!” before trying to shut the window.

“Whoa, hold on a second Hitler.” Penny interrupted, jamming the window with some webbing. “You have something of mine.” J.J sputtered angrily at the webbing in his window. “That was found on my building, it belongs to-“

“Oh, aren’t you just the Paper Boy who killed Valentine’s Day!” Penny accused, “robbing a poor hero-“

“-VIGILANTE!-“

“-of her rose. Shame on you! I hope Cupid shoots you in the head with one of those arrows, maybe then your cold dark heart might experience a little bit of love. Or you know at least kindness!”

“LOOK HERE YOU LITTLE-“

“Yeah, your right. One arrow won’t be enough; I don’t think there’s anything out there that can succeed in such a feat. I’ll be taking my rose, thank you.” Penny webbed the rose over to her, clutching it protectively against her chest. “Hey, that could be have valuable information concerning-“ Jameson started.

Penny scoffed at him, “Puh-lease, it’s a rose J.J, whatcha gonna get out of it? A fingerprint? Blood? Yeah right, there is nothing on this rose that will give away my identity. Now if you’ll excuse me, I have a scavenger hunt to finish.” Penny gave a half-hearted salute to him, and jumped off the building and swung away as Jameson yelled curses at her back.

She stopped a few buildings away, and looked at the rose more carefully. Some of the petals had fallen off, and the bow was crooked-probable from the harsh treatment from J.J. Penny turned and glared at the Daily Bugle building, feeling suddenly protective of her little rose and debated on flipping the finger at the building. But she made it a point to be a good role model, and just in case any kids happen to be watching she didn’t want to be the one teaching that gesture. So instead she lifted up her mask, and stuck her tongue at the building instead.

After she finished mocking Jameson, she turned back to the rose and carefully opened up the card. This one read: _Rooftop that you always go to after you finish kicking bad guys ass_. Okay, so this guy knew her patrol route, or at least they’ve watched her long enough to know which rooftop she always stops at before finishing patrol. And now she was freaked out, because it sounded like she had her own personal Valentine stalker. Which actually seemed like just her luck.

There was a second note attached to the first, and Penny wearily unfolded it. _P.S_ it read, _I am not a stalker_. “Oh how reassuring,” Penny grumbled. “Just like how the killer always answers when you call, or the monster is actually in the bathtub and not under the bed.” She added this rose to her now bouquet, and went to spin a line.

But hesitated once more, and nervously fingered the black chip Tony gave her. She had put it around her neck, using a strand of webs, for safe keeping. She was struck once again for how ridiculous this situation was, Penny still couldn’t believe she was still following this crazy scavenger hunt.

Maybe it’s because she’s been so alone lately, or that she just needed something new in her life. But Penny actually liked her little Valentine’s Day Hunt; it made her feel important and special. Something she hadn’t felt in a while, and if this did end up being a big hoax, then she was definitely kicking some major butt by the end of this night.

Speaking of which, it was getting rather late. Penny just realized how soon the sun would begin to set, she needed to wrap this up quick. Penny glanced at the roses, “You better not be playing me,” she warned them, and shot a web. She set her course toward her favorite rooftop, getting ready for what lay ahead.

 

**Notes for the Chapter:**

> Okay, now that were getting close to Valentine’s Day, and I haven’t updated this in-about a year? I decided to get off my lazy arse and right the next part. Only one more part after this, I’ll probable post it on Valentine’s Day, or before-depends on how much I’m pestered.
> 
> Penny finally gets to meet her mysterious, slightly stalkerish, Valentine’s crush! Of course we know who it is, but will Penny figure it out? Wait and see! Hope you enjoyed!


	5. Sign Her Up!

**Summary for the Chapter:**

> The scavenger hunt comes to an end and Penny finds her mystery man...

**Notes for the Chapter:**

> Hi guys, yeah I know. I said I would post this on Valentines Day, and it isn’t Valentines Day. 
> 
> But I was busy yesterday getting stuff ready for my mom’s dinner party, and updating another thing I was working on. Super sorry, so I guess you guys get the update one day late. But its better than nothing, right?   
> Well anyway, enjoy what I got for you!

**___**

Penny swung through New York toward her designated rooftop. She couldn’t help the nerves gnawing at her stomach, her the odd exciting sensation that washed over her body in waves. As excited as Penny was about finding out who her Valentine’s mystery man is, she was almost hoping this was a hoax. If it ended up being just some random fan, that would be really weird. Besides, Penny wasn’t sure what she would do about that.

Or if it was a villain, at least she could kick their sorry butt ten times over.

But what if it was someone else? Someone who-well Penny wasn’t sure who else. This was fun while it lasted, but right now she was ready to know who was doing this for her. Penny felt her breath catch as her rooftop came into view. She swung quickly and landed on the rooftop, her eyes felt ready to pop out of her skull. “Okay...definitely not a villain.” Penny murmured as she looked around. 

The rooftop had been beautifully decorated. There was a table set up in the middle of it, with a fancy white tablecloth, it had a cute candle-light dinner theme on it, and all around the rooftop had strings of pink, white, and red lights strung and glowing. The sun had gone down, and left the entire roof lighted with color. She had seen it from a far, which is why she swung here to quickly to see.

Her spider-sense wasn’t going off, so it wasn’t a trap-from what she could tell anyway. But whoever had done this, they weren’t here either. Penny stood there, her breath felt whisked from her and her heat beat like a rabbits. Is this what people felt like on Valentine’s Day all the time? It wasn’t a bad feeling…

Then she spotted a note on the table, she stepped forward and gazed at it. It was addressed: To- Spider-Girl and had been placed on one of the plates. There was a bouquet of the spider-themed roses placed on the plate as well. Penny smiled softly, and added her own to the pile; she carefully placed them by her plate and looked around nervously.

It was still deserted, well besides her own presence and Penny wasn’t sure what she was supposed to do. The chip that Tony gave her was in her boot, but it didn’t seem like she needed it. Penny crossed her arms and debated on investigating, but then something caught her ears. It was someone muttering, and cursing and for a moment the lights flickered.

Penny looked around for the noise, before tracking it down to a spot on the far side of the roof that was covered by a sheet. She had noticed it, but was to taken away with the other decorations to REALLY notice. Penny looked around for a moment, just to see if there was anything else that happened to be hiding, before slowly walking forward.

There was a sudden bang, then a curse that would have had a sailor blushing. Penny cleared her throat awkwardly, but it went unnoticed. There was another curse, and Penny cleared her throat again-only way louder. The cursing stopped abruptly, “Uh…what time is it?” someone asked someone very familiar. There was a pause, then another loud curse-followed by a few other loud bangs before none-other than Deadpool stumbled out.

Spider-Girl crossed her arms with a small smile, “Uh…Deadpool? What are you doing here? I thought you had this really big job in Bolivia?” a few months ago, Penny found Deadpool (who had been running out New York after another job) and Penny took it upon herself to watch him and make sure he wasn’t cause TOO much chaos and destruction. Eventually the two had ended up hanging out on this very rooftop after Spider-Girl finished stopping a bank heist, and they shared a hotdog or two. Penny found that the mercenary wasn’t as bad as other heroes said he was, she actually found his presence-enjoyable! But Deadpool said he had this really big job in Bolivia and was gone the next day. Penny thought he was still there, but apparently…

Deadpool shrugged his shoulders, “What can I say? I got bored…” Spider-Girl shook her head and chuckled lightly. “Okay then, but what’s with all this?” she motioned to all decorations and roses. If Penny wasn’t mistaken, she’d say Deadpool looked…nervous? Shy? Dare she say, bashful?

The mercenary scratched the back of his neck shyly, Penny noticed he was wearing a little black bow around his neck, and all his guns looked freshly polished. He actually took the time to wipe away any blood and looked presentable. Sure he still wore the suit, and his guns and swords, but Penny couldn’t help but feel touched. “Well, I remember how you told me your always alone on Valentines-remember we were eating hotdogs and we were both naming things that we hated about life and you said you hated Valentine’s Day-“

“Yeah I remember,” Penny assured.

“Yeah well, I thought that was stupid.-“

“Excuse me?”

“-Because Spider-Girl does a lot for this city, I should know you beat me up whenever I’m trying to kill anyone. So I-“ he shrugged again, “I planned a little…uh…you know…surprise? I guess-for you.” He looked down nervously, his shoe digging aimlessly into the roof. “The roses took forever; I mean I might’ve missed a few thorns-or two. Sorry about that, I didn’t want you to cut yourself so…uh yeah…this wasn’t how I planned on you getting here. But I was having trouble, and I kind of-burnt the tacos…” Deadpool looked like he was trying to get himself to stop babbling, but Penny didn’t mind.

The very thought that Deadpool had planned on this out, heck-the very fact that he cut off the thorns to the roses so she wouldn’t accidentally cut herself touched Penny to the core, and she couldn’t help but feel her heartbeat quicken. But now that she thought about it, it all made sense. Deadpool was still babbling, and looked absolutely mortified with himself. Penny shook her head again and laughed, which cut off Deadpools babble. “Yeah, I guess it wasn’t done very good…” Deadpool muttered.

“No,” Penny said stepping toward him. “No that’s not it. It’s just-goodness Deadpool, this is probable the sweetest thing that ANYONE has ever done for me.” Deadpool perked up a little, his smile shone through his mask. “Really?” he asked like an over-excited toddler.

“Yes,” Penny confirmed, she launched forward and wrapped Deadpool in a hug. He was a couple inches taller than her, so she had to tip-toe to reach his for a full hug. “Thank you,” she whispered. Deadpool hesitantly hugged her back, and Penny would never admit how she liked the way his strong arms fit around her. “Hey no problem baby girl,” he replied, fun and excited tone back. “Anything for the: Friendly Neighborhood Spider-Girl.”

They stayed that way, before Penny realized she had been hugging him for quite a while and sheepishly let go. She tucked and imaginary strand of hair behind her ear, it was a habit she had gotten into whenever she was nervous, excited or shy. But since her mask was on, there was actual no hair there which left Penny blushing even more under her mask; she took a step back.

“Shall we Madame?” Deadpool said formally with a small bow, and gestured to the set up table.

“Yes we shall,” Penny replied using her own formal tone. Deadpool chuckled a little, and held out his arm. Penny shyly took it, and he led her to the table. Penny was astounded by the fact that Deadpool even pulled her chair out for her; she was definitely not used to this kind of treatment. It certainly wasn’t bad…

Deadpool left for a moment, going behind the curtain before bringing out a trey with a covered platter on it. “For today’s special, I have prepare a magnificent feast,” Deadpool announced in one of the worst French accents she’s ever heard, but couldn’t help but laugh with him. Deadpool put down the platter, before uncovering it. It was the charred remains of the tacos Deadpool had been preparing, although something had gone wrong because it was black, lumpy, and barely distinguishable.

It was quiet for a moment as the two stared at the would-be-tacos. Penny picked up her fork and probed he messy remains, “It doesn’t look that bad…” she tried.  

Deadpool scratched his chin, “Well I don’t know how this got here.” He said innocently, he grabbed the burnt food and chucked it over the side of the building thoughtlessly. The moment was followed by the curses of angry pedestrians below, Deadpool looked over the side of the building, “Oops,” he mumbled. “Sorry! Yeah-just walk it off. There you go-that should come right out.” He yelled below. There was another stream of angry words, Deadpool glared and flipped the finger.

Penny allowed her head to fall in her hands, but she was laughing anyway as Deadpool walked back over. “Man, that is one feisty grandma,” he commented. Penny looked at him, “Please don’t tell me you hit an old lady with flying Mexican food.” Penny said.

It was quiet for a moment, “So, how does hotdogs sound?” he asked. Penny sighed and shook her head, but nodded, somehow unable to wipe the smile from her face. “Yeah, sounds great.” She said. She got up from her seat, and walked toward the edge of the building.

Later, around 20 minutes or so, they were back on the rooftop, a dozen hotdogs in hand, and covered in mustard and chili. The two were laughing breathlessly, while fruitlessly trying to wipe chili off their suits. “How was I supposed to know that, that grandma’s niece owned the hotdog stand; talk about coincidence huh?” Deadpool commented.

Penny laughed, “Yeah, who knew she would be at the hotdog stand too. Man your luck is almost as bad as mine,”

Deadpool hummed in agreement as he wiped some mustard off his mask, “Yeah, she had damn good aim too. I mean-wow, I know assassins who aren’t that good.” They burst into laughs again, before positioning themselves on the edge of the building with their bags of hotdogs in hand.

“Well at least the dogs are okay,” Penny pointed out.

Deadpool nodded, “Surprisingly. With how hard the vendor was throwing them at us, I was sure one of them was going to splat on us.”

“Believe me; nothing can ruin a New York hotdog. Nothing.” Penny smiled; she lifted up her mask and bit into her hotdog. Deadpool did the same. When they first had hotdogs, he was a little hesitant about showing his skin. But when Penny didn’t show any discomfort toward it, his courage had strengthened and he was slowly getting comfortable with it.

Penny was glad; she knew he had a skin condition. She could see all the scars around his mouth, but they didn’t seem THAT bad-nothing to get worked up about anyway. Besides, Deadpool had an obvious strong jaw, as well as a great body-when Penny really thought about it…Deadpool had a really great body. Penny suddenly blushed at her thoughts, and looked down at her hotdog and hoped Deadpool didn’t notice and blushing skin.

They enjoyed their hotdogs as they chatted pointlessly, their feet dangled over the side of the building, and a cold breeze would wash over them ever so often, but Penny couldn’t remember when she had been happier. Deadpool just had a way to keep a smile on her face, as well as a way to keep her laughing. It was nice.

Finally their hotdogs were done, and their belly’s full. They quieted down, and listened to the crazy song of New York. Cars honked, people shouted, and lights flashed. Penny still had her mask up above her mouth, but she didn’t mind. She leaned back a little, allowing her muscles to just relax and calm. Deadpool was being suprinsgly quiet, more quiet than Penny had ever heard-or not heard, from him, that and he was staring at her. Did she have crumbs on her face? Penny looked at him questioningly, “Your awful quiet all of the sudden,” she smiled, “What’s on your mind?”

Deadpool snapped out of his quiet state and grinned widely, “Just enjoying my hotdog, nothing beats a New York Chili dog, am I right?” he answered, holding up his half eaten hotdog for emphasis. Penny nodded, and leaned back down again. She sighed in content, and after a moment to turn back to Deadpool.

“Thank you,” Penny told him.

“What can I say, the hotdogs really are amazing. You’d think that they’d be worse, but surprisinglu-“

Penny laughed, “No. Thank you-you know, for this,” she gestured to the decorations and roses. “I usually don’t like that sort of thing, but this…this was really nice. I enjoyed it…thank you.” She looked down a moment later, suddenly shy. Gosh, what was with all these sudden emotions?

Deadpool was quiet a moment longer, before saying, “No prob Bob-well not really, because your names not Bob. Unless it is which is a weird name for a girl-not judging! But yeah, no problem,” he smiled-if possible-bigger. Penny couldn’t help but stare. He had a very nice smile.

Deadpool smirked, “Aw thanks; you have a nice smile too. Way better than mine I bet.”

Penny’s eyes widened, did she say that out loud.

“Obviously,”

And she said that out loud too. Penny groaned and stuffed her face in her hands as she blushed harder. “Oh my gosh…” she muttered, feeling ready to just jump off the building from embarrassment. Deadpool chuckled, and pulled her hands away from her face, “You’re cute when you blush,” he randomly admitted. Which, you know, caused Penny to blush harder. Deadpool scratched his neck, “And now we’re both embarrassed. At least were even…”

Penny chuckled a little, “Yeah, I guess so…” she agreed. She looked up at him, and for a moment they just stared at each other. His scars were fascinating, and he really did have a magnificent smile and-oh now they were leaning closer. And closer, Penny could smell the chili on his costume, and they just kept getting closer. Then suddenly, his lips were on hers in a nervous, but sweet, kiss.

A whole swarm of butterflies infested Penny’s stomach, and she smiled into the kiss. Her nerves were suddenly on fire, and everything seemed to blur her around her, besides the very important fact that she kissing FREAKING DEADPOOL! And FREAKING DEADPOOL WAS KISSING BACK! She almost laughed with glee, the giddy feeling raced up her spine to the tip of her nose, and all the way down to her tingling toe.

Gosh, when did she get to cliché and cheesy.

But Penny didn’t care, because this was perfect.

But then Deadpool pulled away, leaving Penny wanting me. The stupid tease, “If you want to stop…” he whispered nervously “I mean, I’m not the best when it comes to kissing…scars, you know?” Penny shook her head; she wrapped one hand around Deadpools head, and the other around his head. “What the hell are you talking about?” she smiled, “This is my favorite part.” Deadpool smiled with happiness and relief, and Penny pulled his head back down softly.

They were kissing again, but this time Deadpool deepened it. Penny hummed in approval and moved in closer, their legs intertwined, and pressed against the side of the building. There was something…annoying in her boot that was pushing in her leg because of the wall, but Penny paid it no mind. That could wait until after this.

Unfortunately, the universe hated Penny and Deadpool, and wished to make their lives miserable. Because suddenly there was a loud whoosh, Penny’s spider-sense tingled and now the two were surrounded by…the Avengers?! The two pulled away abruptly, Penny had her web-shooters pointed instinctly (but lowered them when she realized who it was), and Deadpool had his pistol out and aimed at Iron Man. “Hey, what’s gives?!” Deadpool demanded.

“Spidey, you okay?” Tony asked, but he seemed uncertain-probable saw what was happening early. “Deadpools not…forcing anything on you, is he?” Cap added.

Penny wished she could just die, just jump off the building and end all embarrassment right here. She hid her face in her hands, attempting to hide her blushing skin. “Yeah,” she squeaked, before clearing her throat. “Yes, I’m fine.” She managed to get out. The thing in her boot, it was the chip Tony gave her. She must have accidently pushed it while they were kissing-well damn it! You couldn’t blame her; she had been brain-fried. Damn you Deadpool, she is blaming him for this!

“You sure?” Cap asked. Penny nodded, refusing to look at any of them. She would not! She could almost feel the smirk of Hawkeye when he said, “Yeah, she’s fine. Just having a little fun, am I right?” Penny groaned loudly.

“Sorry Tony,” she said.

The weapons were still out, but Tony backed away a little. “Well, as long as your absolutely sure…” he said uncertainly. “But seriously Deadpool hurt her and we all hurt you!” Tony threatened.

Deadpool scoffed, but said “Yes Sir,” and saluted goofily. Tony’s glare could be felt through his visor, but none-the-less he dropped his repulsor arm to his side. “Alright, come on guys.”

“Sorry.” Penny repeated. Tony shrugged, “Just remember, you can call us anytime.” He reassured her, glared at Deadpool for good measure, before flying away. The rest of the Avengers followed. When they were gone, Penny still refused to look at Deadpool, she was blushing way too hard for that.

But Deadpool chuckled, and grabbed her wrists to pull her hands away again. “So…what was that about?” he asked.

Penny tried to fight down her blush, but it just wasn’t going. “Don’t worry about it,” she assured him. Deadpool pursed his lips, but shrugged before smiling wickedly. “So, where were we?...”

Penny smiled at him, “Somewhere around here…” she leaned forward to kiss him again, but then a click and flash was heard. Deadpool groaned in annoyance, “Now what?” he demanded. They both looked over to see someone across on the other roof, holding a camera aimed right at them. Penny recognized him; it was another photographer from the Daily Bugle. Now that she thought about it, J.J did have her rose for a bit-he probable read the card. It probably wasn’t too hard spotting the brightly lit rooftop, and connecting the dots.

Well, at least she knew what tomorrow newspaper was going to be about.

“Want me to shoot ‘im?” Deadpool asked.

“No,” Penny answered, “Though I do suggest that we take this somewhere else.” Deadpool smirked happily, “I like that idea.” He approved.

* * *

 

Later Penny climbed back into her apartment through the window. She had her giant bouquet of roses and carefully put them in a cup pull of water. She’s buy a vase for them tomorrow. She was exhausted from the scavenger hunt, but her body still tingled from her time with Deadpool.

She usually wasn’t into that kind of thing, but she really enjoyed her evening. Penny and Deadpool never ended going somewhere else to finish their…time together, but Deadpool did say he would be staying in New York for a few more days, and that they could meet up tomorrow.

That left Penny smiling and unable to wait for tomorrow each time. She smiled to herself as she exchanged her suit in for her pajamas, and couldn’t wipe her smile from her face-even as she fell asleep. If this was a regular thing for Valentine’s Day well…sign her up!

 

**Notes for the Chapter:**

> THE END!
> 
> I was watching “Jessie” in the beginning of this, and wasn’t paying much attention to my writing, so if anything seems weird right there, its because of that. There was probable some OCCness in this, but I tried. Hope you guys enjoyed! Maybe I’ll make a sequel for this sometimes. We’ll see. Bye bye!


End file.
